Water → 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carboxamide trifluoroacetate

HRID 495658Notes

Reaction equation

HRID 495658 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:19]#[N:20])[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]=2[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:7]1=[O:32])[CH3:2].[OH-].[K+].[C:37](=[O:40])(O)[O-:38].[Na+].O>C(O)(C)(C)C>[F:16][C:15]([F:18])([F:17])[C:37]([OH:38])=[O:40].[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:19]([NH2:20])=[O:38])[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]=2[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=2)[C:7]1=[O:32])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 223274103-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile

Product 1

HCID 223273963-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carboxamide trifluoroacetateYield 51%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 3-[2-(diethylamino)ethyl]-2-oxo-7-(trifluoromethyl)-1-[3-(trifluoromethyl)benzyl]-2,3-dihydro-1H-benzimidazole-5-carbonitrile (226.3 mg) in t-butanol (10 ml) was stirred with heating at 60° C. To the solution was added powdered potassium hydroxide crashed in mortar (652.3 mg), and the mixture was stirred with heating at 60° C. for 2 hours. To the reaction mixture were added saturated aqueous sodium bicarbonate solution and water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by HPLC using condition 2 to give the title compound (145.8 mg, 51%).

Workup

  1. additionTo the solution was added
  2. temperaturewith heating at 60° C. for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by HPLC

Sources & evidence

ORD record
ord-a9ca8882835c4f8582dd88f0d78b6d94
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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